Cesium carbonate → N-(1-((6-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)pyridin-2-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79408Notes

Reaction equation

HRID 79408 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[N:26]=2)[N:4]=1)[CH3:2].CS(O[CH2:37][CH:38]1[CH2:42][O:41][C:40]([CH3:44])([CH3:43])[O:39]1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CC(N(C)C)=O>[CH3:43][C:40]1([CH3:44])[O:39][CH:38]([CH2:37][O:31][C:27]2[N:26]=[C:25]([CH2:24][N:5]3[C:6]4[C:11](=[C:10]([NH:12][C:13]([C:15]5[N:19]6[CH:20]=[CH:21][CH:22]=[CH:23][C:18]6=[N:17][CH:16]=5)=[O:14])[CH:9]=[CH:8][CH:7]=4)[C:3]([CH2:1][CH3:2])=[N:4]3)[CH:30]=[CH:29][CH:28]=2)[CH2:42][O:41]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 15570840(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonateHCID 178437935HCID 178437935, compound

Product 1

HCID 67259775N-(1-((6-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)pyridin-2-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamideYield 58.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

To N-(3-ethyl-1-((6-hydroxypyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (17, Step A) (16 mg, 0.039 mmol) in DMA (2 mL) was added (2,2-dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonate (8.2 mg, 0.039 mmol) and Cs2CO3 (25 mg, 0.078 mmol). The reaction vial was sealed and the mixture was heated at 90° C. for 6 hours. The DMA was removed under reduced pressure. The residue was diluted with EtOAc (20 mL). The organic solution was washed with saturated NaHCO3 aqueous solution and brine, and then concentrated under reduced pressure. Silica gel chromatography (DCM/MeOH 10:0.5) gave the product (12 mg).

Workup

  1. customThe reaction vial was sealed
  2. customThe DMA was removed under reduced pressure
  3. additionThe residue was diluted with EtOAc (20 mL)
  4. washThe organic solution was washed with saturated NaHCO3 aqueous solution and brine
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-201f28a51ada4d539f8ea3f962ea3de5
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

Loading…